Hydrochloric Acid → 3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-one

HRID 271304노트

반응식

HRID 271304 반응식
Cl.[Cl:2][C:3]1[CH2:10][CH:9]2[C:11]3(OCC[O:12]3)[CH:6]([CH2:7][CH2:8]2)[CH2:5][C:4]=1/[CH:16]=[CH:17]/[C:18]1[CH:22]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[N:20]([CH3:30])[N:19]=1.C(=O)([O-])O.[Na+]>C1COCC1>[Cl:2][C:3]1[CH2:10][CH:9]2[C:11](=[O:12])[CH:6]([CH2:5][C:4]=1/[CH:16]=[CH:17]/[C:18]1[CH:22]=[C:21]([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)[N:20]([CH3:30])[N:19]=1)[CH2:7][CH2:8]2

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 693065173-{(E)-2-[4-chlorospiro[bicyclo[4.2.1]non-3-ene-9,2'-[1,3]dioxolan]-3-yl]vinyl}-5-(4-fluorophenyl)-1-methyl-1H-pyrazole

생성물 1

HCID 693100833-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-one수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 2N hydrochloric acid (100 ml) and the product of Step 2 (18.0 g, 43 mmol) in THF (100 ml) was stirred at 60° C. for 2 hrs. The reaction mixture was basified with saturated sodium hydrogen carbonate and then extracted with ethyl acetate (3×200 ml). The organic extract was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethylacetate: hexane (1:1) to afford 3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-one (14.96 g, 94%). δH (400 MHz, CDCl3) 1.59-1.71 (2H, m), 1.76-1.83 (1H, m), 2.02-2.10 (2H, m), 2.38-2.51 (2H, m), 2.58-2.62 (1H, m), 2.87-2.90 (1H, m), 2.96-3.01 (1H, m), 3.84 (3H, s), 6.49 (1H, s), 6.64 (1H, d, J 16.5), 7.14-7.18 (2H, m), 7.38-7.42 (2H, m), 7.54 (1H, d, J 16.5).

후처리

  1. extractionextracted with ethyl acetate (3×200 ml)
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting with ethylacetate: hexane (1:1)

출처 및 근거

ORD 기록
ord-4b94b48118254152a5fcdac3e3262050
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452899B2

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